Aryl boronic acid-catalysed dehydrative substitution of benzylic alcohols for C-O bond formation
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A combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C-O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl-substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed-etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the arylboronic acid and oxalic acid.
Estopiñá-Durán , S , Donnelly , L J , Mclean , E B , Hockin , B M , Slawin , A M Z & Taylor , J 2019 , ' Aryl boronic acid-catalysed dehydrative substitution of benzylic alcohols for C-O bond formation ' , Chemistry - A European Journal , vol. Early View . https://doi.org/10.1002/chem.201806057
Chemistry - A European Journal
Copyright © 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/chem.201806057
DescriptionWe thank the University of St Andrews and the EPSRC for the award of a DTA studentship (S.E.-D.). We would also like to thank the EPSRC, University of St Andrews, and CRITICAT Centre for Doctoral Training for financial support [Ph.D. studentships to B.M.H, E.B.M and L.J.D; Grant code: EP/L016419/1]. J.E.T thanks the Leverhulme Trust for the award of an Early Career Fellowship (Grant code: ECF-2014-005).
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